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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:36:49 UTC
Update Date2019-07-23 06:14:29 UTC
HMDB IDHMDB0033840
Secondary Accession Numbers
  • HMDB33840
Metabolite Identification
Common NameDihydro-5-methyl-2(3H)-furanone
DescriptionDihydro-5-methyl-2(3H)-furanone, also known as 4-hydroxypentanoic acid lactone or 4-methyl-gamma-butyrolactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, dihydro-5-methyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. Dihydro-5-methyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862469
Synonyms
ValueSource
4-Hydroxypentanoic acid lactoneChEBI
4-Hydroxyvaleric acid lactoneChEBI
4-Methyl-4-hydroxybutanoic acid lactoneChEBI
4-Methyl-gamma-butyrolactoneChEBI
4-PentanolideChEBI
4-ValerolactoneChEBI
gamma-PentalactoneChEBI
gamma-PentanolactoneChEBI
4-Hydroxypentanoate lactoneGenerator
4-Hydroxyvalerate lactoneGenerator
4-Methyl-4-hydroxybutanoate lactoneGenerator
4-Methyl-g-butyrolactoneGenerator
4-Methyl-γ-butyrolactoneGenerator
g-PentalactoneGenerator
Γ-pentalactoneGenerator
g-PentanolactoneGenerator
Γ-pentanolactoneGenerator
Dihydro-5-methyl-2(3H)-furanoneChEBI
g-ValerolactoneGenerator
Γ-valerolactoneGenerator
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name5-methyloxolan-2-one
Traditional Namegamma-valerolactone
CAS Registry Number57129-69-8
SMILES
CC1CCC(=O)O1
InChI Identifier
InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
InChI KeyGAEKPEKOJKCEMS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-31 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility92.6 g/LALOGPS
logP0.36ALOGPS
logP0.57ChemAxon
logS-0.03ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.73 m³·mol⁻¹ChemAxon
Polarizability10.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012014
KNApSAcK IDNot Available
Chemspider ID7633
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Valerolactone
METLIN IDNot Available
PubChem Compound7921
PDB IDNot Available
ChEBI ID48569
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .